Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole

Schmidt A, Habeck T, Snovydovych B, Eisfeld W (2007)
ORGANIC LETTERS 9(18): 3515-3518.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Thermal decarboxylation converts 1,2-dimethylindazolium-3-carboxylate into indazol-3-ylidene, which reacts in situ with ketones to form stable 1:1 adducts. When the reaction is conducted with aromatic aldehydes in alcohols, redox esterifications to benzoates are observed. Model reactions such as redox esterifications of aromatic aldehydes with sodium alcoholates in the presence of 1,2-dimethylindazolium salt and oxidations of sodium benzylates by 1,2-dimethylindazolium salt to aldehydes lend support to a Cannizzaro-type mechanism of this reaction.
Erscheinungsjahr
2007
Zeitschriftentitel
ORGANIC LETTERS
Band
9
Ausgabe
18
Seite(n)
3515-3518
ISSN
1523-7060
eISSN
1523-7052
Page URI
https://pub.uni-bielefeld.de/record/1632757

Zitieren

Schmidt A, Habeck T, Snovydovych B, Eisfeld W. Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS. 2007;9(18):3515-3518.
Schmidt, A., Habeck, T., Snovydovych, B., & Eisfeld, W. (2007). Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS, 9(18), 3515-3518. doi:10.1021/ol0713739
Schmidt, A., Habeck, T., Snovydovych, B., and Eisfeld, W. (2007). Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS 9, 3515-3518.
Schmidt, A., et al., 2007. Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS, 9(18), p 3515-3518.
A. Schmidt, et al., “Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole”, ORGANIC LETTERS, vol. 9, 2007, pp. 3515-3518.
Schmidt, A., Habeck, T., Snovydovych, B., Eisfeld, W.: Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS. 9, 3515-3518 (2007).
Schmidt, Andreas, Habeck, Tobias, Snovydovych, Bohdan, and Eisfeld, Wolfgang. “Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole”. ORGANIC LETTERS 9.18 (2007): 3515-3518.

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PMID: 17672471
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